Highly soluble Rebaudioside D

ABSTRACT

The invention relates to a process for producing highly soluble compositions containing purified steviol glycosides from  Stevia rebaudiana  Bertoni plant extract, more particularly Rebaudioside D. Obtained highly soluble compositions are useful as non-caloric sweeteners or in combination with sugar or high intensity sweeteners in edible and chewable compositions such as beverages, confectionaries, bakery products, chewing gums and the like.

PRIOR APPLICATION INFORMATION

This application is entitled to the earlier filing dates of, and claimsthe benefit of priority to, U.S. Provisional Application No. 61/422,403,filed on Dec. 13, 2010, and U.S. Provisional Application No. 61/424,798,filed on Dec. 20, 2010, the contents of which are incorporated byreference herein in their entirety.

FIELD OF THE INVENTION

The invention relates to a process for producing highly solublecompositions containing purified steviol glycosides from Steviarebaudiana Bertoni plant extract, more particularly Rebaudioside D.

BACKGROUND OF THE INVENTION

High intensity sweeteners possess a sweetness level many times exceedingthat of sucrose. They are essentially non-caloric and used widely inmanufacturing of diet and reduced calorie food. Although natural caloricsweeteners such as sucrose, fructose, and glucose provide the mostdesirable taste to consumers, they possess high calorie values. Highintensity sweeteners do not affect the blood glucose level and providelittle or no nutritive value.

Stevia rebaudiana Bertoni is a perennial shrub of the Asteraceae(Compositae) family native to certain regions of South America. Theleaves of the plant contain from 10 to 20% of diterpene glycosides,which are around 150 to 450 times sweeter than sugar. The leaves havebeen traditionally used for hundreds of years in Paraguay and Brazil tosweeten local teas and medicines.

At present there are more than 230 Stevia species with significantsweetening properties. The plant has been successfully grown under awide range of conditions from its native subtropics to the cold northernlatitudes.

The extract of Stevia rebaudiana plant contains a mixture of differentsweet diterpene glycosides, which have a single base—steviol—and differby the presence of carbohydrate residues at positions C13 and C19. Theseglycosides accumulate in Stevia leaves and compose approximately 10%-20%of the total dry weight. Typically, on a dry weight basis, the fourmajor glycosides found in the leaves of Stevia are Dulcoside A (0.3%),Rebaudioside C (0.6-1.0%), Rebaudioside A (3.8%) and Stevioside (9.1%).Other glycosides identified in Stevia extract include Rebaudioside B, C,D, E, and F, Steviolbioside and Rubusoside. Among steviol glycosidesonly Stevioside and Rebaudioside A are available on a commercial scale.

Steviol glycosides have zero calories and can be used wherever sugar isused. They are ideal for diabetic and low calorie diets. In addition,the sweet steviol glycosides possess functional and sensory propertiessuperior to those of many high potency or high intensity sweeteners.

Rebaudioside D (CAS No: 63279-13-0), as shown in FIG. 1, is one of thesweet glycosides found in Stevia rebaudiana. Studies show that highlypurified forms of Rebaudioside D possess a very desirable taste profile,almost lacking the bitterness and lingering licorice aftertaste typicalfor other Steviol glycosides.

These properties multiply the significance of Rebaudioside D and attractgreat interest for methods of preparation of highly purified forms ofRebaudioside D. However, highly purified steviol glycosides possessrelatively low water solubility. For example Rebaudioside Athermodynamic equilibrium solubility at room temperature is only 0.8%.

On the other hand, it is well known that Rebaudioside A exhibits socalled polymorphism (Zell T. M., Padden B. E., Grant D. J. W., SchroederS. A., Wachholder K. L., Prakash I., Munsona E. J. (2000) Investigationof Polymorphism in Aspartame and Neotame Using Solid-State NMRSpectroscopy, Tetrahedron, 56, 6603-6616). Rebaudioside A amorphous,anhydrous and solvate forms differ significantly from each other interms of solubility, which is one of the main criteria for thecommercial viability of a sweetener. In this regard, as shown in Table1, the hydrate form of Rebaudioside A displays the lowest solubility(Prakash I., DuBois G. E., Clos J. F., Wilkens K. L., Fosdick L. E.(2008) Development of rebiana, a natural, non-caloric sweetener, FoodChem. Toxicol., 46, S75-S82). It was shown that Rebaudioside A maytransform from one polymorph form to another at certain conditions (U.S.patent application Ser. No. 11/556,049).

TABLE 1 Properties of Rebaudioside A forms (U.S. patent application Ser.No. 11/556,049) Polymorph Forms Form 1 Form 2 Form 3 Form 4 HydrateAnhydrous Solvate Amorphous Rate of Very low Intermediate High (>30%High (>35% dissolution in (<0.2% in 60 (<30% in 5 in 5 in 5 H₂O at 25°C. minutes) minutes) minutes) minutes) Alcohol <0.5% <1% 1-3% <0.05%content Moisture   >5% <1%  <3% 6.74% content

Rebaudioside D possesses even lower water solubility compared toRebaudioside A. In room temperature it can be dissolved only at 0.05%.When heat is applied, one can make up to 0.5% solution, but upon coolingto room temperature, Rebaudioside D will quickly crystallize back outfrom the solution. Considering high sweetness intensity of RebaudiosideD, even 0.05% solubility can be sufficient for many applications.

Many food production processes use highly concentrated ingredient mixesprior to producing final forms of food products. In that case, higherconcentrations of dissolved Rebaudioside D will be required. It has tobe noted that using the heat for dissolution of Rebaudioside D may notbe possible in many compositions which contain heat sensitivecomponents. Also maintaining high temperature of mixture for prolongedtime to prevent premature crystallization of Rebaudioside D can causethermal degradation of mixture components or undesirable changes oforganoleptic properties.

Therefore there is a need for developing highly soluble forms orcompositions of Rebaudioside D which can provide stable solutions withminimal or no heat treatment.

Furthermore, considering the similar chemical structures of RebaudiosideD and other steviol glycosides, as well as other terpene glycosides, thedeveloped approaches may be used in the case of other glycosides aswell.

SUMMARY OF THE INVENTION

The invention relates to a process for producing highly solublecompositions containing purified steviol glycosides from Steviarebaudiana Bertoni plant extract, more particularly Rebaudioside D.

Hereinafter the term “steviol glycoside(s)” will mean Rebaudioside A,Rebaudioside B, Rebaudioside C, Rebaudioside D, Rebaudioside E,Rebaudioside F, Stevioside, Steviolbioside, Dulcoside A, Rubusoside, orother glycoside of steviol and combinations thereof.

Hereinafter, unless specified otherwise the solubility of material isdetermined in RO (reverse osmosis) water at room temperature. Where thesolubility is expressed as “%” it to be understood as number of grams ofmaterial soluble in 100 grams of solvent.

Hereinafter the term “highly purified” will mean purity level of atleast 95% (w/w) on anhydrous basis.

Hereinafter the term “low purity” will mean purity level of less than95% (w/w) on anhydrous basis.

Hereinafter the term “TSG content” will mean Total Steviol Glycosidescontent, and it will be calculated as sum of all steviol glycosides'content including Rebaudioside A, Rebaudioside B, Rebaudioside C,Rebaudioside D, Rebaudioside E, Rebaudioside F, Stevioside,Steviolbioside, Dulcoside A and Rubusoside.

Hereinafter the terms “Reb A, B, C, D, E, F” refer to Rebaudiosides A,B, C, D, E, F, respectively.

Hereinafter the term “Reb D” refers to Rebaudioside D (CAS No.63279-13-0).

Hereinafter the term “crystalline Rebaudioside D” will refer to any formof highly purified Rebaudioside D obtained by crystallization from anaqueous or aqueous alcoholic solution containing Rebaudioside D andfurther separating the Rebaudioside D crystals and drying them by anymeans known to the art.

Hereinafter the term “amorphous Rebaudioside D” will refer to any formof highly purified Rebaudioside D obtained by spray drying or freezedrying of aqueous or aqueous alcoholic solution containing RebaudiosideD.

Hereinafter the terms “non-steviol glycoside fraction” or “non-glycosidefraction” will mean materials predominantly comprising compounds, otherthan steviol glycosides, which are present in the water extracts ofStevia rebaudiana leaves or commercially available stevia extracts atmore than 0.0001% (w/w) on dry basis. Not limiting examples of suchcompounds include typical plant materials, such as pigments andsaccharides, phenolic compounds, volatile oil components, sterols,triterpenes, flavonoids, coumarins, non-glycosidic diterpenes(sterebins) spathulenol, decanoic acid, 8,11,14-ecosatrienoic acid,2-methyloctadecane, pentacosane, octacosane, stigmasterol, bsitosterol,a- and b-amyrine, lupeol, b-amyrin acetate, and pentacyclic triterpeneor combinations thereof. The materials designated as “non-steviolglycoside fraction” or “non-glycoside fraction” and prepared in someembodiments of present invention may also contain small residual amountsof steviol glycosides.

Hereinafter the term “polyol” refers to a compound that contains morethan one hydroxyl group. A polyol may contain 2 to 7 hydroxyl groups.Non-limiting examples of polyols include erythritol, maltitol, mannitol,sorbitol, lactitol, xylitol, inositol, isomalt, propylene glycol,glycerol (glycerine), threitol, galactitol, reducedisomalto-oligosaccharides, reduced xylo-oligosaccharides, reducedgentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup orcombinations thereof.

Hereinafter the term “molasses” refers to sugarcane molasses such asfirst molasses, second molasses, US grade “A”, “B”, “C”, and substandardblackstrap molasses, as well as beet sugar molasses, boil-back molasses,high-test molasses, refiners' molasses, sweet sorghum syrup.Non-limiting examples of typical constituents of molasses are sucrose,glucose, fructose, starch, gums, pentosans, hexitols, myoinositols,mannitol, aminoacids, wax, sterols, phosphatides, aconitic, citric,malic, oxalic, glycolic, succinic, fumaric acids, melanoidins ormixtures thereof.

Hereinafter the term “caramel” refers to class I (INS No: 150a), ClassII (INS No: 150b) class III (INS No: 150c), and class IV (INS No: 150d)caramel colors or mixtures thereof.

In one embodiment of the invention, crystalline Reb D was dissolved in awater ethanol mixture and spray dried to obtain amorphous form of Reb Dwith improved solubility.

In another embodiment, crystalline or amorphous Reb D is combined with apolyol at a ratio of 1:100 to 100:1 (w/w) to obtain a composition withimproved RebD solubility.

In yet another embodiment, the combination of crystalline Reb D andpolyol at a ratio of 1:100 to 100:1 (w/w) is dissolved in water oraqueous alcohol and spray dried to provide a composition with improvedReb D solubility.

In another embodiment, the combination of amorphous Reb D and polyol ata ratio of 1:100 to 100:1 (w/w) is granulated by means of roll compactgranulator. The granulated material made in accordance with the presentinvention advantageously yields a product with favorable characteristicssuch as Reb D solubility and particle size distribution.

In another embodiment, steviol glycosides are separated from Steviarebaudiana leaves' water extract to obtain the non-glycoside fraction ofStevia. Any separation technique known to the art, such aschromatographic separation, crystallization from water or aqueousalcohol, adsorption on specific resins, membrane separation, orsupercritical fluid extraction may be employed.

In another embodiment, amorphous or crystalline Reb D is combined with anon-glycoside fraction of stevia at a ratio of 1:100 to 100:1 (w/w) toobtain a composition with improved RebD solubility.

In yet another embodiment the combination of crystalline Reb D andnon-glycoside fraction of stevia at a ratio of 1:100 to 100:1 (w/w) isdissolved in water or aqueous alcohol and spray dried to provide acomposition with improved Reb D solubility.

In another embodiment, amorphous or crystalline Reb D is combined withmolasses or caramel at a ratio of 1:100 to 100:1 (w/w) to obtain acomposition with improved RebD solubility.

In yet another embodiment, the combination of crystalline Reb D andmolasses or caramel at a ratio of 1:100 to 100:1 (w/w) is dissolved inwater or aqueous alcohol and spray dried to provide a composition withimproved Reb D solubility.

It is to be understood that both the foregoing general description andthe following detailed description are exemplary and explanatory and areintended to provide further explanation of the invention as claimed.

BRIEF DESCRIPTION OF THE DRAWING

FIG. 1 shows the chemical structure of Rebaudioside D (CAS No:63279-13-0).

DETAILED DESCRIPTION OF THE INVENTION

The invention is aimed to provide Rebaudioside D forms or compositionscontaining Rebaudioside D with improved solubility in water.

In one embodiment, highly purified crystalline Rebaudioside D, which hasa solubility of 0.05%, was dissolved in aqueous alcohol at aconcentration of 0.5 to 50%, preferably 5-25%, more preferably 10-20%.The alcohol content used in aqueous alcohol is 0.1-100% (vol/vol),preferably 20-70% (vol/vol), more preferably 30-50% (vol/vol). Thealcohol is selected from the group consisting of alkanols, moreparticularly methanol, ethanol, n-propanol, 2-propanol, 1-butanol,2-butanol or combinations thereof. To dissolve the Reb D, the solutionis heated to 30-100° C., preferably 50-100° C., more preferably 60-100°C. To prevent premature crystallization, the solution is maintained at20-80° C., preferably 30-70° C., more preferably 50-60° C. The solutionis fed to a spray drier to obtain a powder of highly purified amorphousReb D with a solubility of 0.2%.

In another embodiment highly purified amorphous or crystallineRebaudioside D is combined with a polyol at a ratio of 1:1 to 1:100(wt/wt), preferably 1:1 to 1:30 (wt/wt), more preferably 1:1 to 1:10.The polyol is selected from group consisting of erythritol, maltitol,mannitol, sorbitol, lactitol, xylitol, inositol, isomalt, propyleneglycol, glycerol (glycerine), threitol, galactitol, reducedisomalto-oligosaccharides, reduced xylo-oligosaccharides, reducedgentio-oligosaccharides, reduced maltose syrup, reduced glucose syrup orcombinations thereof. Preferably, the polyol is selected from groupconsisting of erythritol, maltitol, mannitol, sorbitol, lactitol,xylitol, inositol, and isomalt, and more preferably, erythritol,maltitol, sorbitol, and isomalt. When the prepared compositionscontaining crystalline Reb D are dissolved in water at room temperaturethe solubility of Reb D is 0.1-2.0%. For compositions with amorphousRebD the solubility under the same conditions is 0.3-2.0%.

In another embodiment, the combination of amorphous Reb D and polyol ata ratio of 1:1 to 1:100 (w/w), preferably 1:1 to 1:30 (w/w), morepreferably 1:1 to 1:10, is granulated by means of any equipment known toart suitable for granulation of fine powder into granules, preferably bymeans of a roll compact granulator. The roll speed was between about5-20 rpm, preferably between about 7-10 rpm, and more preferably about 9rpm. The roll pressure was between about 20-80 bar, preferably betweenabout 40-50 bar, and more preferably about 45 bar. The granulator rotorswere rotating at a rate of between about 50-2000 rpm, preferably betweenabout 100-200 rpm, and more preferably at about 150 rpm. The granulatorswere equipped with screens which sizes were between about 0.5-6.0 mm,preferably between about 1-4 mm, and more preferably about 3.1 mm forthe pre-granulator and about 1.6 mm for the fine granulator. When theprepared compositions are dissolved in water, the solubility of Reb D is0.1-2.5%.

In another embodiment, the non-glycosidic fraction of stevia is combinedwith crystalline Rebaudioside D, at a ratio of 1:1 to 1:100 (wt/wt),preferably 1:2 to 1:20 (wt/wt), more preferably 1:3 to 1:10. The mixtureis dissolved in aqueous alcohol at a concentration of 0.5 to 50%,preferably 5-25%, more preferably 10-20%. The alcohol content in usedaqueous alcohol is 0.1-100% (vol/vol), preferably 20-70% (vol/vol), morepreferably 30-50% (vol/vol). The alcohol is selected from the groupconsisting of alkanols, more particularly methanol, ethanol, n-propanol,2-propanol, 1-butanol, and 2-butanol. To dissolve the Reb D, thesolution is heated to 30-100° C., preferably 50-100° C., more preferably60-100° C. To prevent premature crystallization, the solution ismaintained at 20-80° C., preferably 30-70° C., more preferably 50-60° C.The solution is fed to a spray drier to obtain a powder of highlysoluble Reb D composition. When the prepared compositions are dissolvedin water at room temperature the solubility of Reb D is 0.3-5.0%, or0.1-2.5%.

In another embodiment, molasses are combined with crystallineRebaudioside D, at a ratio of 1:1 to 1:100 (w/w), preferably 1:2 to 1:20(w/w), more preferably 1:3 to 1:10. The mixture is dissolved in aqueousalcohol at a concentration of 0.5 to 50%, preferably 5-25%, morepreferably 10-20%. The alcohol content in used aqueous alcohol is0.1-100% (vol/vol), preferably 20-70% (vol/vol), more preferably 30-50%(vol/vol). The alcohol is selected from the group consisting ofalkanols, more particularly methanol, ethanol, n-propanol, 2-propanol,1-butanol, 2-butanol. The molasses are selected from the groupcomprising of US grade “A”, “B” and “C” molasses as well as substandardmolasses, preferably grade “A” molasses. To dissolve the Reb D thesolution is heated to 30-100° C., preferably 50-100° C., more preferably60-100° C. To prevent premature crystallization the solution ismaintained at 20-80° C., preferably 30-70° C., more preferably 50-60° C.The solution is fed to a spray drier to obtain a powder of highlysoluble Reb D composition. When the prepared compositions are dissolvedin water, the solubility of Reb D is 0.1-3.5%.

In another embodiment, caramel is combined with crystalline RebaudiosideD, at a ratio of 1:1 to 1:100 (w/w), preferably 1:2 to 1:20 (w/w), morepreferably 1:3 to 1:10. The mixture is dissolved in aqueous alcohol at aconcentration of 0.5 to 50%, preferably 5-25%, more preferably 10-20%.The alcohol content in used aqueous alcohol is 0.1-100% (vol/vol),preferably 20-70% (vol/vol), more preferably 30-50% (vol/vol). Thealcohol is selected from the group consisting of alkanols, moreparticularly methanol, ethanol, n-propanol, 2-propanol, 1-butanol,2-butanol. The caramel is selected from the group comprising of class I,class II, class III and class IV caramel colors, preferably, class Icaramel. To dissolve the Reb D the solution is heated to 30-100° C.,preferably 50-100° C., more preferably 60-100° C. To prevent prematurecrystallization the solution is maintained at 20-80° C., preferably30-70° C., more preferably 50-60° C. The solution is fed to a spraydrier to obtain a powder of highly soluble Reb D composition. When theprepared compositions are dissolved in water, the solubility of Reb D is0.3-3.5%.

The following examples illustrate preferred embodiments of theinvention. It will be understood that the invention is not limited tothe materials, proportions, conditions and procedures set forth in theexamples, which are only illustrative.

EXAMPLE 1 Preparation of Amorphous Rebaudioside D

100 g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd,with 98.1% purity (on anhydrous basis) was dissolved in 500 mL aqueousethanol, containing 50% (vol.) ethanol. The solution was maintained at50° C. and dried using a YC-015 laboratory spray drier (ShanghaiPilotech Instrument & Equipment Co. Ltd., China) operating at 175° C.inlet and 100° C. outlet temperatures. The obtained amorphous powder wascompared with crystalline material for solubility.

TABLE 2 Solubility of Rebaudioside D Solubility, % (in water)Temperature Crystalline Amorphous 20° C. 0.05 0.1  50° C.* 0.2 0.5 100°C.* 0.5 1.1 *Solutions obtained at 50° C. and 100° C. crystallized aftercooling down to room temperature (20° C.).

EXAMPLE 2 Preparation of Non-Glycosidic Stevia Fraction

500 g of commercial stevia extract, containing Rebaudioside A 41.2%,Stevioside 30.6%, Rebaudioside C 9.9%, Rebaudioside F 2.3%, Dulcoside A0.5%, Rubusoside 0.6%, Rebaudioside D 1.5%, Steviolbioside 0.2% andRebaudioside B 0.1% were dissolved in 9.5 liter of RO water and passedthrough a column packed with 10 liter Amberlite XAD7HP resin. The columnwas washed with 10 volumes of RO water. The collected water fractionswere evaporated under vacuum at 55° C. and spray dried to yield 45 gpowder with 9.8% TSG including 7.8% Rebaudioside D, 2.0% Rebaudioside Aand non-detectable amounts of other steviol glycosides.

EXAMPLE 3 Preparation of Rebaudioside D Soluble Composition

10 g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, with98.1% purity (on anhydrous basis) was mixed with different amounts oferythritol (Prima Inter-Chem Sdn Bhd, Malaysia). The obtained blendswere tested for solubility, and solution stability to crystallization,during storage at room temperature.

TABLE 3 Solubility of Rebaudioside D blends Blend ratio, wt/wtSolubility*, % (RebD in water) RebD/Erythritol 20° C. 100° C.** 2:1 0.060.09 1:1 0.08 0.2 1:5 0.2 0.5 1:10 0.4 1.0 1:15 0.8 1.3 1:20 1.5 2.0*Solubility is calculated for RebD % content in solution **The materialwas dissolved at 100° C. and cooled down to room temperature (20° C.).The reported concentrations are stable (do not crystallize) for 24 hrsstorage in room temperature.

EXAMPLE 4 Preparation of Rebaudioside D Soluble Composition

10 g of amorphous Rebaudioside D prepared according to EXAMPLE 1, wasmixed with different amounts of erythritol (Prima Inter-Chem Sdn Bhd,Malaysia). The obtained blends were tested for solubility, and solutionstability to crystallization, during storage at room temperature.

TABLE 4 Solubility of Rebaudioside D blends Blend ratio, wt/wtSolubility*, % (RebD in water) RebD/Erythritol 20° C. 100° C.** 2:1 0.080.09 1:1 0.16 0.2 1:5 0.4 0.5 1:10 0.9 1.0 1:15 1.0 1.3 1:20 1.1 2.0*Solubility is calculated for RebD % content in solution **The materialwas dissolved at 100° C. and cooled down to room temperature (20° C.).The reported concentrations are stable (do not crystallize) for 24 hrsstorage in room temperature.

EXAMPLE 5 Preparation of Rebaudioside D Soluble Composition

10 g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, with98.1% purity (on anhydrous basis) was mixed with different amounts oferythritol (Prima Inter-Chem Sdn Bhd, Malaysia). The obtained blendswere dissolved in 5 volumes of aqueous ethanol, containing 50% (vol.)ethanol. The solution was maintained at 50° C. and dried using a YC-015laboratory spray drier (Shanghai Pilotech Instrument & Equipment Co.Ltd., China) operating at 175° C. inlet and 100° C. outlet temperatures.The obtained amorphous powder was tested for solubility, and solutionstability to crystallization, during storage at room temperature.

TABLE 5 Solubility of Rebaudioside D blends Blend ratio, wt/wtSolubility*, % (RebD in water) RebD/Erythritol 20° C. 100° C.** 2:1 0.160.2 1:1 0.3 0.4 1:5 0.6 0.7 1:10 1.2 1.4 1:15 1.5 1.8 1:20 1.8 2.5*Solubility is calculated for RebD % content in solution **The materialwas dissolved at 100° C. and cooled down to room temperature (20° C.).The reported concentrations are stable (do not crystallize) for 24 hrsstorage in room temperature.

EXAMPLE 6 Preparation of Rebaudioside D Soluble Composition

10 g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, with98.1% purity (on anhydrous basis) was mixed with different amounts ofstevia non-glycosidic fraction prepared according to EXAMPLE 2. Theobtained blends were tested for solubility, and solution stability tocrystallization, during storage at room temperature.

TABLE 6 Solubility of Rebaudioside D blends Blend ratio, wt/wtSolubility*, % (RebD in water) RebD/Non-glyc. fraction 20° C. 100° C.**1:2 0.07 2.1 1:1 0.06 1.5 2:1 0.06 1.3 3:1 0.06 0.8 4:1 0.06 0.3 5:10.05 0.15 *Solubility is calculated for RebD % content in solution **Thematerial was dissolved at 100° C. and cooled down to room temperature(20° C.). The reported concentrations are stable (do not crystallize)for 24 hrs storage in room temperature.

EXAMPLE 7 Preparation of Rebaudioside D Soluble Composition

10 g of amorphous Rebaudioside D, prepared according to EXAMPLE 1, wasmixed with different amounts of stevia non-glycosidic fraction, preparedaccording to EXAMPLE 2. The obtained blends were tested for solubility,and solution stability to crystallization, during storage at roomtemperature.

TABLE 7 Solubility of Rebaudioside D blends Blend ratio, wt/wtSolubility*, % (RebD in water) RebD/Non-glyc. fraction 20° C. 100° C.**1:2 0.1 2.1 1:1 0.09 1.5 2:1 0.08 1.3 3:1 0.06 0.8 4:1 0.06 0.3 5:1 0.050.15 *Solubility is calculated for RebD % content in solution **Thematerial was dissolved at 100° C. and cooled down to room temperature(20° C.). The reported concentrations are stable (do not crystallize)for 24 hrs storage in room temperature.

EXAMPLE 8 Preparation of Rebaudioside D Soluble Composition

10 g of crystalline Rebaudioside D was mixed with different amounts ofstevia non-glycosidic fraction, prepared according to EXAMPLE 2. Theobtained blends were dissolved in 5 volumes of aqueous ethanol,containing 50% (vol.) ethanol. The solution was maintained at 50° C. anddried using a YC-015 laboratory spray drier (Shanghai PilotechInstrument & Equipment Co. Ltd., China) operating at 175° C. inlet and100° C. outlet temperatures. The obtained amorphous powder was testedfor solubility, and solution stability to crystallization, duringstorage at room temperature.

TABLE 8 Solubility of Rebaudioside D blends Blend ratio, wt/wtSolubility*, % (RebD in water) RebD/Non-glyc. fraction 20° C. 100° C.**1:2 0.4 2.5 1:1 0.3 2.1 2:1 0.2 1.8 3:1 0.1 1.4 4:1 0.08 0.9 5:1 0.060.4 *Solubility is calculated for RebD % content in solution **Thematerial was dissolved at 100° C. and cooled down to room temperature(20° C.). The reported concentrations are stable (do not crystallize)for 24 hrs storage in room temperature

EXAMPLE 9 Preparation of Rebaudioside D Soluble Composition

10 g of crystalline Rebaudioside D, produced by PureCircle Sdn Bhd, wasmixed with different amounts of molasses (Chee Lam Trading, Malaysia).The obtained blends were dissolved in 5 volumes of aqueous ethanol,containing 50% (vol.) ethanol. The solution was maintained at 50° C. anddried using a YC-015 laboratory spray drier (Shanghai PilotechInstrument & Equipment Co. Ltd., China) operating at 175° C. inlet and100° C. outlet temperatures. The obtained amorphous powder was testedfor solubility, and solution stability to crystallization, duringstorage at room temperature.

TABLE 9 Solubility of Rebaudioside D blends Blend ratio, w/wSolubility*, % (RebD in water) RebD/Molasses 20° C. 100° C.** 1:2 0.53.5 1:1 0.3 2.6 2:1 0.2 2.1 3:1 0.1 1.6 4:1 0.09 1.2 5:1 0.08 0.5*Solubility is calculated for RebD % content in solution **The materialwas dissolved at 100° C. and cooled down to room temperature (20° C.).The reported concentrations are stable (do not crystallize) for 24 hrsstorage in room temperature

EXAMPLE 10 Preparation of Granulated Rebaudioside D Soluble Composition

1 kg of amorphous Rebaudioside D prepared according to EXAMPLE 1, wasmixed with different amounts of erythritol (Prima Inter-Chem Sdn Bhd,Malaysia). The obtained blends were transferred to an Alexanderwerk WP50N/75 roller compactor. The compactor was operating at 9 rpm and 45 barpressure. The compacted mass was fed to a pre-granulator and a finegranulator with rotors at rotating at 150 rpm. The screen size for thepre-granulator was 3.1 mm and for the fine granulator was 1.6 mm. The“overs” (particles that are too large) and “fines” (particles that aretoo small) were separated by top screen having a screen size of US Mesh10 and bottom screen of US Mesh 40. The % ratio of“overs”:“product”:“fines” was 0.9%:78.2%:20.9% respectively. Theobtained products were tested for solubility, and solution stability tocrystallization, during storage at room temperature.

TABLE 10 Solubility of Rebaudioside D blends Blend ratio, w/wSolubility*, % (RebD in water) RebD/Erythritol 20° C. 100° C.** 2:1 0.090.1 1:1 0.17 0.2 1:5 0.4 0.6 1:10 0.9 1.2 1:15 1.0 1.8 1:20 1.5 2.5*Solubility is calculated for RebD % content in solution **The materialwas dissolved at 100° C. and cooled down to room temperature (20° C.).The reported concentrations are stable (do not crystallize) for 24 hrsstorage in room temperature

While the foregoing has described one or more embodiments of the presentinvention, it will be understood by those skilled in the art thatvarious changes and modifications may be made and equivalents may besubstituted for elements or compositions thereof without departing fromthe true scope of the invention. Therefore, it is intended that thisinvention not be limited to a particular embodiment disclosed, but thatthe invention will include all embodiments falling within the scope ofthe appended claims.

The invention claimed is:
 1. A method of preparing a highly solubleRebaudioside D composition, comprising the steps of: a. providing afirst composition comprising Rebaudioside D; b. providing a secondcomposition comprising at least one component selected from the groupconsisting of: a non-glycosidic fraction of Stevia; molasses; andcaramel color; c. dissolving the first and second compositions in asolvent selected from the group consisting of water or aqueous alcoholto make a solution; and d. spray drying the solution to obtain thehighly soluble Rebaudioside D composition, wherein said Rebaudioside Dcomposition has a water solubility of at least about 0.05% at 20°C. 2.The method of claim 1 wherein the second composition comprises anon-glycosidic fraction of Stevia at a ratio (wt/wt) of thenon-glycosidic fraction of Stevia to the first composition of about1:100 to about 100:1, preferably about 1:2 to about 1:20, morepreferably about 1:3 to about 1:10.
 3. The method of claim 2 wherein thenon-glycosidic fraction of Stevia is prepared by a process comprisingthe steps of: providing a stevia extract; dissolving the stevia extractin water or aqueous alcohol to form a stevia extract solution; passingthe stevia extract solution through a chromatographic system packed withmacroporous adsorbent resin capable of adsorbing steviol glycosides;collecting an effluent from the chromatographic system; and drying theeffluent to obtain the non-glycosidic fraction of Stevia.
 4. The methodof claim 3, wherein the stevia extract contains about 10-95%, preferablyabout 30-90%, and more preferably about 40-85% total steviol glycosides.5. The method of claim 3, wherein the water or aqueous alcohol ratio todissolved stevia extract solids (vol/wt) is about 1:1 to about 200:1,preferably about 5:1 to about 100:1, more preferably about 10:1 to about50:1.
 6. The method of claim 3 wherein the amount of stevia extractexceeds an adsorption capacity of the adsorbent in the chromatographicsystem by about 1-10 times, preferably by about 1-5 times, and morepreferably by about 1-1.5 times.
 7. The method of claim 3, wherein thechromatographic system comprises about 1-20 consecutively connectedcolumns, preferably about 1-10 columns, and more preferably about 1-6columns.
 8. The method of claim 1, wherein the second compositioncomprises molasses at a ratio (w/w) of molasses to the first compositionof about 1:100 to about 100:1, preferably about 1:2 to about 1:20 andmore preferably about 1:3 to about 1:10.
 9. The method of claim 8,wherein the molasses is selected from the group consisting of: sugarcanemolasses such as first molasses, second molasses, US grade “A”, “B”,“C”, and substandard blackstrap molasses; beet sugar molasses; boil-backmolasses; high-test molasses; refiners' molasses; sweet sorghum syrup;and a combination thereof.
 10. The method of claim 1, wherein the secondcomposition comprises caramel at a ratio (w/w) of caramel to the firstcomposition of about 1:100 to about 100:1, preferably about 1:2 to about1:20, and more preferably about 1:3 to about 1:10.
 11. The method ofclaim 10, wherein the caramel is selected from the group consisting ofClass I (INS No: 150a), Class II (INS No: 150b), Class III (INS No:150c), and Class IV (INS No: 150d) caramel colors and combinationsthereof.
 12. The method of claim 1, wherein the drying step comprisesspray drying the solution in a spray drier operating at an inlettemperature of about 150-200° C. and an outlet temperature of about80-120° C.